


well this is awkward

by jhoom



Category: Supernatural
Genre: Age Difference, First Kiss, Frottage, M/M, Masturbation, Mistaken Identity, Strangers to Lovers, Sub/Dom undertones, Writing Prompt Wednesday, implied bottom!dean, mutual masturabation, office!AU, past aaron/dean (mentioned), voice!kink
Language: English
Status: Completed
Published: 2016-09-30
Updated: 2016-10-03
Packaged: 2018-08-18 15:21:36
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 8,428
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8166584
Author URL: https://archiveofourown.org/users/jhoom/pseuds/jhoom
Summary: Mr. Novak frequently calls in to IT for help with his computer.  Dean offers to field all his calls because there's something about the guy's voice that just gets him going...





	1. Chapter 1

**Author's Note:**

> this is part of [unforth](http://archiveofourown.org/users/Unforth)'s [Writing Prompt Wednesday](http://archiveofourown.org/works/7056115/chapters/16040662). the other day i saw this prompt and could **not** let it go
> 
>  **prompt:** Alright…but…you just have a really sexy voice, okay? So I called tech support, and you said, “Hello my name is…” and I just had to keep you talking as long as possible, and my problem wasn’t actually too serious but I pretended it was just so I could get your extension. And then I called back. And then I called back again. Even though my computer problem was fixed. And you just seem to keep flirting with me over the phone? And the more we talk, the more I think things I shouldn’t? And okay this is the creepiest thing I’ve ever done but I miiiight be masturbating while we’re talking and I just have to keep you from finding out. Must not moan!
> 
> first chapter could probably stand alone (even though it lacks *some* closure), but i'm silly and like to make things longer than necessary and will be adding a bit more after. tags are currently only for the first chapter though.
> 
> and as always, feel free to come bug me on [tumblr](http://jhoomwrites.tumblr.com)

Mr. Novak from Marketing was probably the _worst_ at anything electronic that Dean had ever encountered.  And considering the average age of company employees was 55, that was really saying something.  The guy’s first day and he has to call Dean for help.  He was trying to set up his computer (and Dean immediately made a note to check with Ash why the hell his computer wasn’t already set up for him when he came in) and couldn’t tell the difference between an Ethernet port and an HDMI hook-up.  

Dean rolled his eyes, explained the difference and talked him through the process of telling the two apart.  (Like seriously?  How did this need to be explained, they had completely different sizes and the fact that Novak had somehow managed to get the rectangular HDMI cable wedged into the square ethernet port had Dean both baffled and impressed.)  By the end of the conversation, Dean was confused whether the guy was some old dude who hadn’t had his own working computer until well after he’d graduated from college.  No way a guy anywhere this side of forty could be _that bad_ at computers.

(Plus you don’t get a voice that deep and gravelly unless you’ve been chain smoking two packs a day for at least a few decades.)

After helping Novak work out the problem, he politely gave him his private extension in case he ever had any future issues.  The guy seemed thankful enough and wasn’t offended that Dean had basically said he expected to hear from him on a weekly basis.

Life went on as usual, the only change being the addition of Novak’s frequent calls to IT.  Dean still worked with Charlie and Ash on fixing server problems and trying to set up wi-fi in the lobby and meeting rooms.  He still hung out with Jo and his brother on weekends.  Still made time to work on his car and binge watch Netflix.  The slight increase in his incoming calls didn’t matter at all.

Until there was a whole two weeks where Novak didn’t call a single time.  The guy couldn’t go more than a couple days without needing help troubleshooting surprisingly simple tasks.  Installing new drivers, connecting his printer, burning a CD, all of these mundane tasks Dean didn’t normally think required an explanation because they were so _intuitive_ to him.  

Honestly, for a while Dean thought the guy was pulling his leg and making up the problems.  But the sincere gratitude at the end of each call made Dean second guess the assertion.  Poor guy genuinely didn’t have a clue.

So when the calls abruptly stopped, Dean was worried.  He told himself each day before going home that he was definitely _not_ disappointed Novak hadn’t called and definitely did _not_ miss hearing his voice.  

By the time the third week rolled around, he’d basically given up hope of hearing him again.  Maybe he found someone on his floor to help him out with his random little computer troubles.  Maybe he learned how to use Google.  Maybe he didn’t like talking to Dean so he’d switched to one of the other IT people (and Dean had to forcibly bite his tongue a few times to keep from hounding Charlie and Ash about it, knowing full well they would _never let it go_ ). 

So when he picked up his phone while fiddling around with some code for a side project, he genuinely didn’t expect the voice that greeted him on the other end.

“Dean from IT, how can I help you?”

“Hello Dean.”

And holy _shit_.  It was probably because it’d been so long since he heard from Novak, but fuck if his voice didn’t sound sex rough and delicious.  Dean jerked a bit in his seat as shockwaves of those words bolted straight to his dick.  

“Mr. Novak,” he choked out, hopefully not sounded as turned on as he inexplicably was.  

“I realize this may seem like a silly question-”

“Dude, I _told_ you,” Dean cut off, so glad to fall back into their normal routine because _fuck_ did he need a distraction.  “No stupid questions.  It’s stupid to have a question and not ask it.  It is literally my job to be here and help you.”

“Thank you, Dean.”  The smile in his voice made Dean start to picture the lips attached to it.  Not helping.  “It’s just, I haven’t used my computer in a few weeks and-”

“You were out for a few weeks?”

“Yes.  I’m sure you noticed you had much more free time at work, since I wasn’t there to pester you.”  Dean started to argue with him about that, but the teasing note to Novak’s voice stopped him.  “As I was saying, while I was on vacation my password expired and-”

“Where’d you go on vacation?”

_What the actual fuck, Winchester?  What.  The actual.  Fuck.  Are you doing?_

The line went silent for a second and Dean bit his lip, waiting to jump in and apologize, but then the other man went on as though this were a completely normal part of their talks.  “My parents live in California and I took some time off to visit them and my siblings.”

“Hey I got a brother who moved out to California after college.” 

They went on and on like that, chatting.  And while it did a bit to take the edge off of Dean’s embarrassing lack of control ( _where did that even come from?_ damn he needed to get laid), it did nothing to diminish the crush he now realized he was starting to develop on the other man.  

“Dean,” Novak interrupted a story about Sam jumping off the shed as a kid, though not unkindly.  “I would love to continue this, but unfortunately I have a meeting in an hour and still need to get into my computer.”

“Oh, right right right.”  Thank god this was over the phone so Novak couldn’t see him blush.  “I’ll reset your password to the system default, once you log in with it you’ll be prompted to update it.”  He started typing the necessary keys when he could already hear the question coming.  “Default password is your date of birth, no 0’s before the month or date, just the last two digits for birth year.”   

“Thank you, Dean.”

“No problem, Mr. Novak.”

When he hung up, his ear was warm from the receiver and his hand itched to dial Novak’s extension to hear his voice some more.  

It spiraled out of control from there.  The calls came every couple days again, starting with a quick chat where the deep richness of Novak’s voice hit Dean like a ton of bricks, even the times he knew to expect it.  The chats grew longer and longer until one of them had to apologize and shift them back to Novak’s problem du jour.  Half the time they were quick fixes, not warranting the hour they’d lost talking to each other.  The half of the time, they were issues Dean had already talked him through in the past.  Either the guy had a shit memory (doubt it, he could remember every detail Dean revealed about his personal life like it was nothing), or maybe Dean’s crush wasn’t completely one-sided.

Speaking of crushes, whatever it was going on with Novak only gets worse once he started to find out more about the guy.  He didn’t have anything else to go on since he’d never met the guy in person, but he started having really detailed fantasies about that voice directing him how to touch himself.  Fantasies he found himself retreating to more and more before going to bed at night or in the shower before work.  

And then there was the flirting.  The ever so casual flirting that Dean couldn’t remember starting but definitely engaged in whenever possible.

“Oh, you run?  Bet you got killer thighs.”

“You’re going to France for Christmas?  Gonna hit up any of those nude beaches?”

“Holy crap, you got _five_ brothers?  So you the hot one or the smart one?”

Novak never side-stepped any of the comments, never indicated he wasn’t interested.  If anything he’d flirt back and that really wasn’t helping Dean’s willpower or professionalism.  

The breaking point hit about a month later.  He was on the second floor helping one of the guards with a security camera that kept acting up.  Up on a ladder right next to the elevator, he had the pleasure of greeting everyone in Human Resources as they came back from lunch or meetings with the (literal) higher ups.  

Dean had almost finished up when the doors opened for the next batch of people returning to work.  He nodded to Garth and Jody as they came in, midday coffees in hand, but then nearly fell off the ladder when he heard a voice drift out to him.

“I bet you like it rough, don’t you Novak?”  Balthazar, that was definitely Balthazar.

“I’m sure there’s something inappropriate in what you’re implying, but yes I prefer it rough when I go hiking.  Difficult terrain is more challenging.”

“Darling, you make it sound like I was trying to be _subtle_.”

The rest of the conversation was lost to him as the doors glided shut, leaving him with the very real  picture of Novak saying such things as _inappropriate_ and _i prefer it rough._

He wasn’t proud of it, but he did a half-assed job of finishing up with the security camera, then rushed back to his floor.  There was a small private bathroom tucked away in the back, and he more or less sprinted in and locked the door behind him.  It was the first time (and only, he swore, definitely _only_ time _)_ he ever jerked off at work.  

Hell, it was over pretty much before it started.  Novak leading him through the woods, tiring Dean out on some trail.  And then finding some secluded corner, nothing but the wild and them, telling Dean to brace himself against a tree before undoing his pants and-

Aaand that was as far as Dean got before he came all over himself and the bathroom sink.  Ugh, at least he hadn’t gotten any on his pants.

Okay, he probably should’ve known the ‘only time’ thing was bullshit.  Because the _inspiration_ for his little masturbatory session was still very much a part of his work week.  He now regularly had to excuse himself after his calls with Novak to take care of the raging boner he got from even the blandest of topics.  He’d heard people say that they could listen to some guys read the phone book and be turned on, he just hadn’t found a voice like that before Novak. 

Dean was aware of how inappropriate the whole thing was, but he’d only ever toed the line of being an outright perve.  The most he did while on the phone with Novak was maybe palm his crotch or readjust his dick for better comfort.  Sure, he was hard from the second he heard Novak speak, but he wasn’t _actively_ jerking off or anything.  That had to count for something.

At least until September 18th.  He remembered the date very distinctly because that was the day he well and truly descended into hell.

He’d _like_ to be able to put the blame on Ash.  It was Ash who got him riled up in the first place, sending him that joke email with nothing but gifs of chicks and dudes in varying states of undress.  Basically all porn, with a shitty joke about how this is the closest Dean was getting to sex and an offer to buy him lube for his next date with his right hand.

(Unfortunately, it all seemed to be true.  Since this whole Novak thing started, Dean hadn’t exactly been picking anyone up like he normally did.  His libido was through the roof, but his interest was very narrowly focused on one man.)

Joke or not, Ash had _spectacular_ taste in porn and Dean spent a good half hour perusing the images.  (In his defense, he was in his cubicle and everyone else was in a meeting.  If there were any chance he’d be caught, he would’ve saved them for when he was at home that evening.)  So he already half-hard when his phone rang.

“Dean from IT,” he answered absentmindedly, scrolling back to the gif of the dark-haired twins going at it.

“Hello Dean.”

Oh fuck.  Fuck fuck fuck fuck _fuck_ not _now_.

Mouth suddenly dry, he swallowed before choking out, “Hey, Mr. Novak.”  

“I hope this isn’t a bad time?”

 _Yep_.  “Nope.”   _Worst timing.  Oh god I’m going to do something stupid.  I’m going to do something really stupid._ “What can I do for you today?” 

“What can you do for me today,” he repeated with an almost sing-song lilt to his voice.  Oh god, now he had the mental image of him on his knees in front of the guy, arms behind his back and looking up at him as he asked for directions on how to please him.  And yeah, now his hand was definitely toying with the buckle of his belt.  “Well, I was hoping you could help me locate some files I saved but seem to have misplaced.  They’re not in the Documents folder or on the Desktop.”

“Uh huh.”  He did his best to listen to the words themselves instead of the buttery thick voice saying them.  As Novak went on and on about his usual file saving habits, Dean lost the willpower to resist temptation and decided to just go for it.  

He kept goading Novak into telling him more irrelevant details, all while unzipping his pants enough to get his hand on his dick.  He’d already figured out the problem by the time he was jerking off in earnest, phone propped between his shoulder and ear as one hand stroked the shaft and teased at the head, the other hand slipping down to gently fondle his balls.  

Biting the inside of his lip, he managed to direct his groans into almost normal sounding mmhmm’s and uh huh’s.  Or at least if he didn’t do a good job of it, Novak didn’t comment.  With that perfect sex voice goading him on, all Dean had to do was imagine himself on his knees under Novak’s desk.  Jerking himself off just like he was now, the only difference was there’d be a cock in his mouth and fingers threaded through his hair, the slightest of pressure on the back of his head to keep his pace steady.

“Dean?”

“Yeah?” he grunted.   _So **close** , c’mon keep talking._

“What should I do?”

_Bend me over a table and fuck me?  Use my mouth until I’m choking on your come?  Tie me to your chair and use me however you want?  Fuck I am so yours, I’ll do whatever you want if you **just keep talking**._

“Sounds like…”  His voice was hoarse so he coughed and tried again.  “Sounds like since you downloaded it from an email, it’s likely in your Downloads folder.  You can get it from the File Explorer, it should be one of the pinned folders there.”

He deserved all the awards ever for being able to speak coherently at a time like this.  This was seriously the most impressive moment of Dean’s entire sex life and it kinda sucked that he’d never be able to brag about it without feeling like a creep.

“Oh, I didn’t even think of that.”  Through the phone, Dean could hear clicking.  “There it is.  Thank you, Dean.  As always, you’ve done an excellent job assisting me.”

_So good for me, Dean.  You’ve done an excellent job, letting me fuck that pretty hole of yours._

Dean dropped the phone and gasped through his climax, ripped out of him so suddenly that the sheer force of it almost made him pass out.  He blinked a few times before registered the panicked voice on the other end of the phone.

“Dean?  Dean is everything alright?  I heard a crash-”

Limbs numb and heavy, he fumbled for the phone where it’d landed.  “Yeah, I uh… I just dropped the phone.  Sorry ‘bout that.”  Even his tongue was heavy and didn’t want to move.  His lips barely formed the words, his whole body shutting down in the wake of his orgasm.  He felt almost drunk, or at least pleasantly buzzed and couldn’t find it in him to care about what he’d just done. 

“Oh.  It’s alright, I’m glad you aren’t hurt.”

“Definitely not hurt,” he laughed, pronouncing each word with either too many or too few syllables.  Now that it was over - both his impromptu jerk-off session and the computer troubles - Dean found he still didn’t want the moment to end.  “You got big plans for the weekend?”

“Yes, actually.”  And he listened to Novak go on about some museum exhibition he was excited about and the charity event they were holding to raise funds for the new wing.  Dean once again hmm-ed and oh-ed his way through the conversation, but this time he was drowning in the softness of Novak’s tone.  God, it was like being wrapped in a warm blanket in front of the fire and Dean could seriously get used to it.

When the call finally ended, Dean could’ve almost pretended the whole thing was some really vivid hallucination induced by his current dry spell.  At least if it weren’t for the splotches of come all over his pants and boxers (fuck there might even be a stain on the carpet).  Sitting at his desk, he finally started to come down from his post-coital daze.  The whole time, a single thought kept rattling through his head.

What the fuck just happened?

**Notes for the Chapter:**

> i'm going to pretend for a second that i know how long this will be and say there's going to be one more chapter *crosses fingers that it doesn't end up more* the plan is to throw in some two-person love triangle nonsense because dean is such a oblivious bean sometimes
> 
> (and yes, i *did* throw a dcj reference in there)
> 
>  **bonus scene: later that day**  
>  charlie: dean, can you help me with this?  
> dean: sure.  
> dean: *keeps sitting there, doesn't even turn away from his desk*  
> charlie: ... okay but like are you gonna come over and look at the problem  
> dean: ... can you send me a screenshot?  
> charlie: ... why won't you get up  
> dean: ... i assure you i have a good reason and that you really don't want to know what it is  
> charlie: ...  
> dean: ...  
> charlie: ... okay i'll send the screenshot


	2. Chapter 2

**Notes for the Chapter:**

> probably three chapters? *fingers crossed* probably jumping to more than just good ol' deansturbation in the final chapter

Admitting to himself that he’d jerked off while talking to some unsuspecting dude on the phone was bad enough.  He felt so guilty he avoided his desk (and by extension his phone) as much as possible for the remainder of the week.  He’d even lost the will to jerk off on his own time in the safety of his apartment.  

But he couldn’t avoid his work and slack off forever, so he sucked it up and forced himself to spend all of Friday at his desk.  With no calls (well, there were plenty of calls, but none from Novak), he felt he’d regained some of his composure and would be able to act more appropriately whenever Novak _did_ end up calling him next.  Because it was inevitable, now, that he’d be hearing from the deep voiced Marketing agent.  

And because life just wasn’t fair to Dean Winchester, another wrench was thrown into his wreck of a work environment.  

All this happened about the same time Dean got called up to help with installing a new copier onto the server.  As he walked through the cubicle maze on the fifth floor, nodding at a few people he recognized, he did a double take and nearly collided with a potted plant when he saw the cute new intern the Marketing team got.  

Blue eyes and messy hair and _young_ , probably several years younger than Dean.  Neatly pressed slacks and a button down shirt with a deep blue tie to match his eyes and _fuck_ he stubbed his toe when he hit the damn plant.  Nursing his wounded pride and limping a bit, he pulled his eyes away from the hottie and pointedly marched to the copier.  With laser focus a job like this didn’t really warrant, he got the copier set up in record time and marched right back to the elevator to escape.  

It was on his mind all day, an inescapable itch to… well he wasn’t sure what, but it was almost certainly going to get him into as much trouble as the whole Novak situation.  

That day at lunch, he plopped his tray down across from Charlie and groussed, “Jesus, what’s with the Marketing division?  They get the _hottest_ guys working for them.”

“I assume you mean Cas?” Charlie said as she opened her yoghurt.

“Who?”

“Cas.  Castiel, actually, but he’s over there sitting next to Balthazar and Crowley.”  She gestured with her chin before slurping up a big spoonful of yoghurt.

Dean turned (none too subtly, he realized later, but oh well) and saw the dark-haired intern from earlier.  His eyes lingered, tracing over his body.  In truth, he’d meant _both_ Novak and the intern equally, but the less he said about Novak the better.  Charlie was already suspicious after the _incident_ and she was impossible to throw off once she got a whiff of some good gossip.  

Going with it, he shrugged and tried not to blush.  “He ain’t bad looking,” he admitted, stabbing his pasta with his fork.  “What do you know about hot guys, anyway, Bradbury?”

“Uh, excuse you?  Just because I dig the ladies doesn’t mean I don’t know hot when I see it.  And Cas is _hawt_ with a capital H.  Obviously I wouldn’t personally tap that, but I wouldn’t mind watching him like go for a run or lift heavy things in front of me or wear tight shirts.”

“Yeah well… your face is hot.”

“Seriously, Winchester?”  She looked both bewildered and amused.  “You gotta work on your comebacks or deflections or _whatever the hell_ that was.”  She dug back into her yogurt, pushing aside a chunk of strawberry in favor of a blueberry.  “I have that on good authority from the other girls working the fifth floor that he’s currently single.”  And she waggled her eyebrows for good measure.

“Ugh, don’t ever make that face again.”  

Charlie rolled her eyes but went back to her snack.  After a few minutes of silent brooding, Dean forced himself to ask, “And have you heard from the girls on the fifth floor if he’s into dudes?”  He winced at how fucking obvious and desperate that was (and maybe a little because it felt like he was really just trying to avoid the Novak issue by jumping at the next available person).

“That… I unfortunately don’t know.  But I could try to find out.”

“Oh god _please_ don’t.  Doesn’t Becky work fifth floor?  If she finds out you’re asking for me, she will be ten times more insufferable than she already is.  Remember when she thought I liked Aaron?”

“Uh, you did like Aaron.”

“Not the point.  She totally scared him off by asking him about me and talking to him about me and generally giving him the impression that I’m a total creep.”  Remembering his little jerk off session a few days ago, he admitted there was some truth to that description.  

“Okay, fine, fair point.  You could always just go talk to him and find out for yourself.”

“Maybe I will,” he said, even as he knew he wouldn’t.  Having a crush on the cute intern was about as bad as having a crush on the older Marketing exec.  But at least the phone stuff kept his crush relatively hidden.  

Novak called later that day, some basic question about if they had a certain program (they did) and if the new projectors were up in the conference room (they weren’t).  It wasn’t awkward at all, much to Dean’s relief.  Not that it should’ve been.  It’s not like Novak _knew_ what had happened and as long as Dean wasn’t weird about it, things could go back to normal.

Not that he knew what normal was anymore.

A sort of equilibrium eventually grew.  Dean would flirt with the intern Cas whenever he happened to see him across the cafeteria.  He’d make eye contact and wink, loving how the kid would blush and duck his head before shyly waving back.  Occasionally, when he got the chance, he’d gently bump into him as he walked by.  Nothing more than the casual brushing of arms or shoulders, but enough to get Cas’ attention and too quick for him to do more than gape after him.  It was fun and harmless and satisfied something he didn’t realize he’d been missing out on.

Then when Novak would call, he’d get all his flirty conversation needs filled.  Before Dean thought he was imagining it that Novak would flirt back, but he seemed to be getting bolder and bolder, dropping compliments and the occasional suggestive line that made Dean hot under the collar.

“You’re so smart and talented, Dean.  I’m lucky to have your help.”

“Thank you again, Dean.  Do you give out all the troubling computer newbies your personal extension, or just me?”

“Fixing up a car sounds like hard work.  You must be good with your hands.”

(That last one sent him straight to the bathroom after the call, embargo on work jerk-off sessions be damned.)

Sinking heavily into his chair after that made him realize the only thing lacking in his little dual crush situation.  

Sex.

He still hadn’t had sex in months and his frequent masturbation sessions didn’t do much to take the edge off, especially not since… well, _since_.  Weighing the pros and cons, he allows himself to slip back into his old routine of jerking off at work.  Something about _being there_ adds to the thrill and is almost satisfying.  The proximity to both Novak and Cas, the risk of being caught, it mixed together in this weird adrenaline rush that got him off way faster than it had any right to.

Junkie that he was, it was only a matter of time before it escalated from there.

One fine Thursday afternoon, Dean pretty much had to bolt from the cafeteria after seeing Cas bend over to retrieve the water bottle he’d dropped.  His mind and dick immediately sprang into action at the image right in front of him.  He’d turned on his heel and got back to his floor as fast as the elevator would let him.  

Which was actually not that fast.  It stopped on every floor on the way up and then he got cornered by Adler, a guy who viewed himself as Dean’s boss simply because he had a higher clearance and title but no actual power.  The guy pulled Dean into his office to help with plug in the damn cord for his monitor, as though the guy thought such a menial task was too beneath him.  And Dean knew damn well the guy knew how to do it, he was being an ass and wasting Dean’s time just because he could.

Cursing under his breath as he stormed back to the elevator before changing his mind and sprinting up the remaining two flights of stairs instead.  Heaving the door open, he was about to march off to the bathroom when he realized his phone was ringing.  Because _of course_ it was.

Torn briefly between the two, he groaned and walked over to his cubicle with his shoulders slumped.  Mentally preparing himself for some ridiculous follow-up from Adler, he snapped out a gruff, “What?”

“Dean?”  Uncertainty tinged the familiar voice.  “Is this… is this a bad time?”

“Mr. Novak…”  He felt instantly flustered as his dwindling arousal spiked back up.  He looked around to make sure he was alone and figured he’d take this as a sign.  Sitting back in his chair and unbuttoning his pants, he dropped his annoyance and answered, “Perfect timing, actually.  What can I do for you?”

Novak hesitated for a moment, deciding whether or not Dean was merely being polite.  “Well, I was wondering if you could help talk me through some of the issues I’m having with Excel.  I’m used to an older version but this new update has me really lost.  I know it might not be something you normally handle-”

“Mr. Novak, I would love to personally _handle_ any problems you have.”  Finger spreading precome while he played with his slit, Dean did his best to keep his words clear and even.  “Go ahead and walk me through what you’re trying to do and I’ll help out as best I can.”

And then in unnecessary detail, Novak described every aspect of the reports he was trying to create and the data he needed to input.  The serious almost authoritative tone his voice took on when he spoke about the Marketing side made Dean nearly groan in appreciation.  But he held back all the noises and somehow managed to stay coherent enough to kind of answer the guy’s questions.  

Admittedly, Dean wasn’t being terribly helpful, but talking about the issues seemed to give Novak ideas on how to solve them.  With minimal input on his part, the few issues were quickly resolved and Dean was still a good couple minutes away from coming.  In frustration he said the first thing that sprung to mind.  

“Tell me a story.”

“Pardon?”

“Just… tell me a story.  I haven’t heard from you in a while and I missed the sound of your voice.  Tell me… tell me about your weekend.”

The silence rung out long enough that Dean was worried he’d pushed too hard and made it weird.  Yeah they often talked personal stuff, but there must have been something off about the way he’d said it that made Novak want to hang up on him.  He half-expected the dial tone any second now, but instead the gravelly sound of Novak echoed from the receiver.

“Sure, Dean.  I’d be happy to tell you about my weekend.”  And it was a surreal experience to come while listening to a guy talk about a marathon he ran two towns over, a guy he’s never even seen before and who can make him hard with just the cadence of his voice.  

Dean sighed in contentment when the call ended.  As fucked as the situation was, it wasn’t like he could pretend he didn’t like it.  

The real problem, he realized on his drive home, wasn’t the spontaneous jerkoffs sessions or the stain on his pants.  It was the distinct image of Cas the intern all sweaty and tan with his messy hair and a rosy tint to his cheeks as he ran a marathon… well, that’d probably been the tipping point that’d made him come.  As fucking hot as Novak’s voice was, it was the association with the intern’s lithe form running that damn marathon.

Dammit was he fucked.

**Notes for the Chapter:**

> lol i don't know why lately i've been making dean so oblivious but the poor guy really needs to get a clue...


	3. Chapter 3

**Notes for the Chapter:**

> when cas calls dean for help with his printer, i want you to picture [this](http://destielonfire.tumblr.com/post/151302628971/supernatural-s09e06-heaven-cant-wait-humancas) while it's happening (except replace slushie goo getting all over the place with paper) thanks to [destielonfire](http://destielonfire.tumblr.com) for gif-ing that scene for me in my desperate attempt to illustrate how adorably flustered cas is

Once Dean established that he had a problem and was a total perv, it became a lot easier for him to just _give in_.  Whenever he thought he could get away with it, he’d take the opportunity to masturbate while on the phone with Novak.  If Charlie or Ash happened to be around, he’d deal with being comfortably hard for the duration of the call.  But after a reasonable amount of time had passed (five or seven minutes, he’d always set a timer, too), he’d slip away from his desk and to the bathroom.

And it wasn’t only about Novak, either.  He kept up the flirtatious gestures and smiles whenever he caught Cas’ eye in the cafeteria.  And on the days he didn’t, he used it as a chance to drink in his fill of the cute intern, memorizing every line of his body for more jerk off fodder later.  Some days he wondered if he should work up the nerve to actually go _talk_ to the kid, but the kid was nearly a decade younger than him and he felt kind of weird about it.  

(Never mind that he was always surrounded by the other fifth floor Marketing types.  Dean’s worst nightmare was walking up to Cas and having Novak be around, listening in.  Because he definitely had a thing with Novak - even ignoring the whole jacking it to the guy’s voice - and asking out the guy’s office intern right in front of him would put a huge damper on… whatever it was they had.)

( ~~Assuming they had something.~~ )

( ~~Stop overthinking it, Winchester.~~ )

It was getting so damn bad that he rigged up his phone to his computer headset so he could record his calls with Novak.  He meticulously saved each conversation and transferred them to his cell phone every afternoon before heading home, replaying them in the car and before he went to bed.  The only thing that made him eventually stop was a strange, super confusing dream where Novak was instructing him on how to bend Cas over his desk and fuck him senseless.

_Maybe in another lifetime, Winchester.  No way you’re lucky enough to get **one** of them, never mind **both**._

~~It only stopped him from listening to the recordings, not from actually making them.  He had a sizeable collection that the day he knew he’d break and binge them while furiously trying to break his all time orgasm record.~~

Dean now spent most of his time at work either stressed out and on edge or far too mellow and relaxed.  Both extremes earn him raised eyebrows from Charlie and Ash, but for better or worse they refrain from commenting.  Thank god, because what the fuck would he even say?  

_“Yeah, no fucking shit I’ve got a short temper right now, Novak hasn’t called lately so I haven’t gotten the chance to come in days.”_

But as always, Novak eventually came through.  After successfully bribing Charlie to take care of the fax machine issue on the seventh floor and Ash to go grab them lunch from that place three blocks down, Dean smiled smugly to himself and then turned his full attention to Novak.  Or rather, maybe about forty percent of his attention was focused on solving his tech problems (and yeah, that’s probably a generous estimate) while the other sixty percent was very busy jacking himself off.  

But as was typically the case these days, Novak’s problem didn’t take more than a few minutes to solve.  Even with Dean being less than articulate and otherwise preoccupied, he could only stall for so long.  Somehow - and fucking thank whatever god of masturbation was looking out for him - after he diagnosed the problem as a corrupt flash drive, he managed to get Novak on the topic of his college days.  Which _somehow_ lead to the story of a guy he dated and _that_ got him talking about the time the two of them almost had sex in the backyard of some frat house.

“You ever had sex in a public place before, Dean?”

He bit his lip and teased his balls before moving back to stroking himself, wondering the whole time if this counted.  “Don’t think you’re supposed to ask questions like that, Mr. Novak.”  Fuck, did he sound breathless?  Hopefully Novak would take it as surprise and not a sign of what was really going on.

“Answer the question, Dean.”

He shivered at the deep vibrato that laced that command and his dick jerked in response.  Still not sure if semi-public jerking off counted, Dean wasn’t sure how to answer.  “Can’t say that I have, but can’t say I’d be opposed to it either.”

“Hmm,” was the only answer he got for a long moment, and Dean got the distinct mental picture of Novak at his own desk, dick in hand, jerking himself off just like Dean was a few floors up.  Admittedly, it was most likely Dean’s imagination running away with the remote _possibility_ of Novak being as turned on as he was.  But the illusion is shattered when Novak kept going, voice too smooth and in control.  “I suppose the same goes for me.  Though if it hadn’t started raining, the story would end quite differently…”

Dean wanted to add that he wouldn’t be chased off by the rain.  That if Novak ever wanted him, anywhere, he could have him.  Dean would be more than happy to offer himself up if only-

He came with a surprised gasp and accidentally hung up on Novak.  After scrambling to grab some tissues and get himself reasonably cleaned up, he called back to apologize.  Novak just laughed it off and thanked him for helping once again.  

(As a side note, Dean kept perfecting the fantasy.  He kept picturing the intern Castiel whenever he jerked off, thinking about if only _that_ voice and _that_ body were joined together, how it’d be the personification of all of Dean’s wet dreams since puberty wrapped into the perfect embodiment of sex itself.  But as good as the mental image was, he knew Novak’s voice was probably at least a whole octave too low for a guy that young.  Too bad.)

Things started to get out of hand mid-January.  He’d kept up the casual flirting with Cas but then one day at lunch, the intern had caught Dean’s eye then very deliberately indicated the empty space next to him.  Dean had stood there, frozen in his tracks, before being a coward and ducking out of the cafeteria.  And no, okay, he was _not_ avoiding the damn place for the week or two after that.  He was just trying out some new recipes and had a lot of leftovers so he didn’t _need_ to go to the cafeteria, alright?

~~And yeah, he felt like an ass when he _did_ go back and the kid wouldn’t make eye contact with him.  Fuck, he was letting his fantasies interfere with the very _real_ guy who was interested in him.  But the idea of hearing the guy’s voice and having it not sound like Novak’s filled him with such dissonance that it made him feel queasy.~~

And the Novak side of things wasn’t any better.  Novak kept coming up with excuses to call, and Dean was starting to get the suspicion that they were just that.  Problems he’d already helped solve came up again, along with issues that were readily fixed with a quick computer reboot (something he’d trained Novak early on to do first and foremost).  And although Dean was flattered, loved thinking Novak liked talking to him as much as he liked talking to Novak, he felt ill at ease when Novak started asking him to _come to the fifth floor_ and show him how to fix things in person.  

Now, no one could ever say that Dean Winchester wasn’t excellent at deflecting.  He dodged each of Novak’s attempts to see him in person, feeling like an ass each time because there was no ignoring the slight disappointment when Novak sighed and accepted the rebuff for what it was.  

And Dean knew damn well that he’d dug himself this hole.  That he had two great guys that might be into him, and he couldn’t commit his mind to actually pursuing either of them because he’d done such a marvelous job of weaving them together in his head.  He couldn’t begin to pick them apart now (believe him, he’d tried), at least not without ruining the idea of being with either of them.  

So he resigned himself to his pervy jerkoff sessions while talking to Novak and thinking of Castiel.  

On January 24th, he groaned when he arrived at his cubicle and saw it basically buried in streamers and balloons.  It did bring him a bit out of his floundering mood (one that kept tailspinning despite his best efforts), even if it meant having to clear out a space for him to work.  There was a note on his computer promising him birthday pie at lunch (along with a scolding postscript from Charlie suggesting none too nicely that he invite the cutie from marketing to have a slice and stop pining after him).  

As a special birthday gift, Ash had even routed all the incoming IT calls to his and Charlie’s desk, leaving Dean free to ‘dick around at his computer’ all day.  (Dean had glared suspiciously at Ash when he’d said that, but eventually decided the guy wasn’t trying to _imply_ anything.)  

(Fat chance of that happening, anyway, since the extra calls meant that Ash and Charlie weren’t going anywhere any time soon…)

Just before lunch, Dean’s startled out of his online poker game by his phone ringing.  Must be someone with his personal extension.  He clicked out of the game window and took the call.  

“Dean from IT, how can I-”

“Dean!  I… I need help-”

“Mr. Novak?”  

He can barely hear the guy, even as he yells into the receiver.  What’s coming across is the sound of way too fast printing and the fluttering of paper hitting the floor, the crisp crumpling of sheets as Novak no doubt tried to grab them before they fell.  It sounded like pandemonium (or at least the office equivalent).  

“The printer it won’t… I can’t get it to stop…  It’s _possessed_ , Dean, I can’t… Please, I need help.  I’m in office 514-”

“Wait, you mean _go down there_?” he snapped and instantly regretted it.

“Dean, _please,_ ” he begged.  “There are five reams of paper in this thing!  I can’t…  I know you don’t want to see me, but _please_ Dean.”

Mouth suddenly dry, Dean licked his lips, clenched his hands, then stood up.  “I’ll be right there.”

It was the worst damn elevator ride of his life.  His leg kept twitching and he felt like he wanted to vomit.  Because this was it.  The illusion was about to be shattered.  There was no going back to the nice, simple status quo he’d worked so hard to maintain.  But Novak needed his help and at this point it’d be a dick move to ignore him.  

As he marched through the fifth floor, he kept his eyes down as he navigated the cubicles and headed to the offices along the east wall of the building.  He dreaded seeing Castiel right now, because _seeing_ Novak and _hearing_ Castiel on the same day would be the absolute _worst_.

512… 513… 514.  

Not that he needed the office number, as it turned out.  The sounds he’d picked up over the phone were amplified now that there was only a flimsy sheet of wood keeping them at bay.  He reached for the doorknob, mentally shielded himself against disappointment, and then barged inside.

“Castiel?” he choked out, stepping into a whirlwind of papers.

Castiel looked up with wide-eyes and an armful of papers, almost on the verge of tears.  

This strange sense of disappointment barely had time to settle (after all that he wasn’t even going to get to _meet_ Novak? had he chickened out and sent one of his interns in to deal with the mess instead?) before Dean sprang into action.  He carefully stepped across the papers littering the floor and dodged the near constant spray from the printer, worked his hand around to the power cord and gave a hard yank.  

The machine hissed in annoyance before shutting down, sending a last stream of paper to the ground as its lights blinked out.  

“Jesus, Cas, what the hell happened in here?” he asked from his knees.  He grabbed the nearest sheets and tried to stack them together, but it barely made a dent in the mess.  It’d take the rest of the day for the poor kid to clean it up.

The intern gapped at Dean a few times before he hugged the papers to his chest and whispered, “You actually came.”

The pit of his stomach dropped because _did he just hear…?_  No, that wasn’t possible.  Get it together, Winchester!

“What?”  He got up and dusted off his pants needlessly just so he’d have something to do with his hands.

Castiel visibly swallowed.  “I…”  He swallowed again (fuck if it wasn’t hot, but Dean valiantly ignored that stray thought) and spoke a little more loudly.  “I didn’t think you’d actually come.  You’ve… you’ve been avoiding me since that time in the cafeteria.  Th- thank you.  I don’t know why I didn’t think of unplugging it though…”  As he trailed off, his cheeks flushed slightly in embarrassment.  

Not that Dean really noticed.  His brain had stopped functioning around the first few words the guy uttered in that too familiar voice.  

It was a total mind fuck.  He’d always assumed Novak was a solid decade older than him, maybe more.  Experienced and put together and able to maybe teach him a thing or two.  Now here he was face to face with the guy, and he was probably nearly that much _younger_ than him.  Fresh out of college, working his first real job…

“Castiel Novak?”  

It wasn’t that Dean was an idiot or anything, but he needed confirmation of his suspicion before he did something crazy.

“Yes?” he asked and squinted at Dean in confusion.  “Dean, are you alright, you look-”

But Dean was already crowding into Cas’ space.  He cradled Cas’ cheeks with his hand and asked, “Can I kiss you?”

Cas nodded.  They met halfway as Dean leaned down the scant two inches between them, rubbing their noses briefly before seeking Cas’ lips.  And fuck did he taste good.  Castiel followed the movement of Dean’s lips, mirroring them before gaining confidence and rubbing his tongue along the seam.  Dean groaned and opened up to him.  He revealed in the taste.

Somewhere along the way, Cas lost his hold on the papers and they scattered to the floor around them.  Taking advantage of the extra space, Dean stepped in even closer.  Castiel stepped back, then again and again until he was backed up into his desk as Dean followed close behind.  

“What are you going to do?” Cas asked between kisses, never moving far away so that his lips moved against Dean’s even as he spoke.

“Do you have lube?”  There was no point in beating around the bush.  He had Cas boxed against his desk and they were both aware of how hard the other was.  

“No.  I _did_ , but I ran out the last time I called you-”

Dean’s head snapped back so he could catch Castiel’s eyes and gage if he was teasing him or not.  But there was nothing but shy honesty there.  Laughing a bit, Dean rested his forehead against Cas’.  “You uh, you jerked off while talking on the phone to me, Novak?”

“What?  No, I… I would _never_ …  It never even crossed my mind.”  He spread his legs and Dean slotted himself between them.

“I may have been doing the same thing.”

Castiel bit his lip but it did nothing to stop the moan that followed that admission.  “ _Fuck_ , Dean, you can’t just say shit like that unless you want… want me to…”

“And if I do?”

They didn’t say much after that, rutting against each other and nipping at each other’s lips with whispered warnings to keep it down.  Cas came first, arching into Dean’s touch until he sighed in relief and collapsed against him, a limp dead weight.  

“Cas,” Dean whined, kissing the top of his head.  “Please-”

“Shhh,” Castiel soothed, threading his hand through the hairs on the nape of Dean’s neck.  “Let go, it’s alright.  You can come.”  The sound of his voice with his other hand he palms at Dean’s cock was all he needed to push him over the edge.  Crying out in relief, Dean nearly collapsed to the ground.  Instead Cas’ hands were there to slow him down and guide him down to the mess of papers.  

Dean let himself be pushed onto his back and opened his arms to allow Castiel to wedge himself in the space between him and the desk.  “You sure made a mess,” he mumbled into the other man’s forehead as he kissed it.  

“You were humping me too, Dean.”

“Kinda meant all the paper, but yeah that too.”  

Cas hit his shoulder but didn’t pull away.  “I’m glad you finally showed your face down here.  I was beginning to think you weren’t interested in more than flirtation.”

“Oh, I’m definitely interested.”  He sighed, knowing that sooner or later he’d have to fess up.  He decided to go with _later_ on most of the details.  “I was kinda nervous, I guess?  That maybe the phone chemistry wouldn’t carry over?”

“I had a similar concern.”  Castiel started to pull away.  Dean resisted the movement at first, but when Cas remained firm he let him go.  “Luckily I have a spare pair of pants in here somewhere,” he muttered to himself as he started looking through his desk drawers.  

“Yeah.”  Dean winced as he stood up.  There was a definite stain on the front of his dress slacks, but the dark material did a halfway decent job of hiding it.  As long as he angled himself properly for the rest of the day, no one would notice.  

He watched as Cas striped down to his boxers in front of him, then quickly changed pants.  Once done, he tossed the dirty ones aside.  Then he appeared right back in Dean’s arms, kissing along his jaw before nosing in at his throat.  Damn this felt nice.  

Dean encircled the younger man in a hug and squeezed tightly.  From this close, he wasn’t nearly so small as Dean had initially assumed.  The guy would probably fill out a bit as he got older, but there was no mistaking the adult proportions he’d dismissed from halfway across the cafeteria.  Feeling curious, he couldn’t help but ask, “How old are you anyway?”  

“23.”  He rolled his eyes at Dean’s obvious surprise.  “I know, I’m young, but I’m good at what I do and I _earned_ this office-”

“Whoa, didn’t mean to imply anything.  I uh, I mean I guess I _did_ think you were an intern the first time I saw you.  But yeah, no, I know you’re wicked smart.  A total moron with computers, but you definitely seem to know your marketing stuff.”

Cas broke the hug to swat playfully at Dean’s hold on him.  “I’m not a _total_ moron.  I can at least type without looking at the keys.”

“A man after my own heart.”

More jabs, this time at his belly.  “How old are _you_?”

“30.  Wait, no, 31 I guess.”  At Cas’ raised eyebrow, he shrugged.  “It’s my birthday.”

“It’s your birthday?” he repeated.  “As in today?”

“Yeah.”  Dean held his breath, wondering if now that the age gap was out there it’d be a dealbreaker for Cas.  It obviously wasn’t for Dean, not when he thought Novak was in his 50’s and not when he saw how young Castiel looked.  

“Oh.”  Castiel had a considering look on his face.  “Can I take you out for dinner tonight?  To celebrate?  Unless you have other plans, of course-”

“Cas?”

“Yes, Dean?”

“I’d like that.   _A lot_.”

The most beautiful smile Dean had ever seen broke out on Castiel’s face.  “It’s a date, then.”

**Notes for the Chapter:**

> "Which somehow lead to the story of a guy he dated and that got him talking about the time the two of them almost had sex in the backyard of some frat house." --> totally a reference to my sku verse btw ;)
> 
>  **bonus scene:**  
>  cas: … the whole time you thought i was some old guy?  
> dean: no of course not why would i- no, nope not even once did i think-  
> cas: *bitchface*  
> dean: yeah okay maybe a little, but to be fair, no one your age should be that terrible at computers  
> cas: *sternly* you also were flirting with phone me at the same time you were flirting with cafeteria me  
> dean: you have a hot voice and a hot body, how can i be blamed???  
> cas: …  
> dean: wait, so this whole time you knew who i was, and thought i was flirting with both phone you and cafeteria you… and YOU didn’t say anything?? like ‘hey i saw you eye fucking me at lunch the other day, why didn’t you stop by to say hello?’  
> cas: *blushes* well, you see, you’re very very attractive and uh… i was intimidated by the prospect of face to face interaction, especially when we were doing so well with the phone calls…  
> dean: …  
> dean: tell me more about how pretty i am


End file.
